Sodium Hydroxide → 4-(2,6-Diethyl-4-methylphenyl)-5-hydroxy-2,6-dimethyl-3(2H)-pyridazinone

Participants

Reaction Steps

To a 25 mL volume three-necked flask with Dean-Stark, 4-(2,6-diethyl-4-methylphenyl)-2,6-dimethyl-5-methylsulfonyl-2,3-dihydro-3-pyridazinone ((2-34)-(1)-39) (1.31 g), toluene (4.55 ml), tetrabutylammonium bromide (61 mg), and 48 w/w % of aqueous sodium hydroxide solution (1.25 g) were added under a nitrogen atmosphere. Water was removed by azeotropic distillation under atmospheric pressure for 22 hours. The reaction mixture was cooled to room temperature, added water, and washed with toluene. To the resulting aqueous layer, 10 w/w % of hydrochloric acid was added to adjust pH to less than 3. The precipitated crystals were collected by filtration, washed with water and dried under reduced pressure to give 0.949 g of 4-(2,6-diethyl-4-methylphenyl)-5-hydroxy-2,6-dimethyl-2,3-dihydro-3-pyridazinone ((1-4)-(1)-39).

Provenance & Evidence